When the Dragon meets the Outlaw
by Gunslinger245
Summary: Six months after Drago's defeat. Hiccup and Toothless go on an expedition and get lost in a storm. Nearly frozen to death, they stumble upon a man named Dutch Van der Linde, who takes them into his gang and becomes one of them. In fear that they'll be exposed, they both decide to stay with them. But as time passes, they'll have no choice but to see their new friends fall apart.
1. Chapter 1:Redemption

**Hey everyone. So yeah, this is my first fanfic with Red Dead Redemption 2. I have some ideas about what's gonna happen throughout this story. But if you have any suggestions that are helpful, please say so in the review section bellow. And another thing, like I always say in my stories, I DON'T OWN ANYTHING. But I have a feeling that you all know that. So I'll go easy. Alright, hears chapter one. Enjoy.**

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It was cold. Too cold. Probably the worst of coldness for young chief Hiccup and his trusted companion Toothless. They stood out in the freezing temperatures of the blizzard and had no other choice but to deal with it. They were suppose to be doing a quick discovery expedition to the northern parts of the archipelago. Unfortunately, their curiosity has left them to go far North than they already have.

They left two weeks ago, leaving Astrid and Valka in charge of running the village while they were out. And much to Hiccup's surprise, the divine winds have brought back some old memories. At that point they traveled across endless ocean for weeks. There was nothing but open seas for miles. Eventually they found some islands to rest before pushing on.

It was only a month before they finally stumbled upon something that they both have never seen. It was a beautiful stretch of land. But it was no island, for it continued for miles and miles on. They continued to fly closer to it until they ran into what seemed to be a small town. And unlike a viking village or market, it was different. There were stone-like structured buildings that covered the shorelines of a lake. Giant boat like objects floated in the waters bellow, but it was not like any viking ship they have seen.

Within the town, there was one street that was covered in an peculiar substance that neither Hiccup or Toothless could make out. On this substance were carts and wagons that were pulled by horses. Some they never knew. And yet the people, they looked different too. For they dressed differently and weren't like any viking outfit they saw in their entire lives.

At first, they saw it as a peaceful yet majestic sight. But once they got closer to the ground, it all turned into a living nightmare. First there was nothing. Not one sound that came out from that small town. Then, shots were heard. It was nothing that they have ever seen. But after that first sound, many more followed. When they took a closer look, they saw an army of guys in strange outfits wielding strange types of weapons shooting at another group of guys.

When they decided to get out of there, they started shooting at them. They evaded them as much as possible, but Toothless was struck one of his forepaws with one of those shots. The impact of the shot was enough to put the Night Fury into a traumatic state of shock, which forced them to lose control and crash land into the forest just outside of the town. Only to be attacked once more by that same group of people. They both ran, and eventually lost them in the mountains. Which was probably the worst idea Hiccup had ever had.

Because it was the coldest storms they have ever been through. And there was no point in flying, because the wind was picking up too fast. And Night Furies can't survive out in cold conditions for too long. So they had to find a place fast.

"We really did it this time, bud,"he sighed. "This storm is worst than we thought."

Toothless lets out low warble in response and gives Hiccup a look.

"Hey, don't blame me for this!" Hiccup narrowed. "It's not my fault those men showed up. We didn't even see them coming."

Toothless shoots another look at his companion before looking back at the path they came from. Then he looks back at Hiccup, who came to a moment of moral realization.

"Okay,"he said. "I'll admit, it was my idea to head up into the mountains. But we had no other choice. And you know that. If we didn't loose those men than we'd be dead sooner or later."

Toothless lets out a throaty, dismissive sound before he continued to walk alongside his friend. They both knew that they made the right call to go into the mountains, but if those men don't kill them soon, then the storm would do it first. It was freezing cold from what they both experienced. And it never stopped.

"How's that arm doing , Toothless,"he asked his dragon.

The young alpha lifted his left paw, which was still wrapped up with some cloth. There were blood marks from what Hiccup saw, but that was a sign that he wasn't bleeding again.

"It doesn't look that bad,"he said. "When we find some shelter we'll try to fix that. But don't die on me yet bud. We're not done here."

Toothless snorted before walking once more. He preferred that those people shoot him dead back there. Because there's no other death that was worse than freezing in the coldest of temperatures.

They continued to walk for dozens of miles, seeing nothing but endless snow. But then, Hiccup saw something in the sky. It was smoke that was arising from a very long distance. And at that moment, he knew that there had to be some shelter close by. He turns to his companion next to him, who was almost frozen to death.

"Come on bud,"he said. "Just a few more miles and we'll find a place to stay out of the storm."

The Night Fury lets out a small coon before pressing on with his best friend. It was harder on him then it was on Hiccup. He's been the one who was doing all the shooting and flying, and now he might freeze faster than his human friend. For he wasn't built for this type of weather. Due to reptiles being cold blooded creatures.

They continued to walk towards the area where the smoke was coming from. Half way there, Hiccup questioned if it was the right place to go residents of the camp would probably be alarmed by their mere presence. But it was something that he had to do. Because if he didn't, then the two won't be able to last through the night.

Once they were there, they spotted an old cabin that seemed to be forgotten. Hiccup looked around to see if anyone else was there before advancing towards the door. But before he did so, he turns back to his partner.

"Stay here Toothless," he commanded. "I think they'll be less intimidated if they only saw one of us."

Toothless nodded in agreement before holding his position. From there, Hiccup proceeded to head into the cabin. On his way, he saw a number of corpses in the snow just outside the place. They laid there lifeless with holes in their heads. He cringed just by seeing the bodies. He had never seen such things like this before. Not even back on Berk.

He took one step on the porch before he noticed something. The house was on fire. He takes a few steps back before looking back at Toothless, who was twenty feet away. He gave him a look before the Night Fury shrugged. Guess they had to find somewhere else to get warm. Because this building was gonna come down faster than any wooden building back at home.

But before he could even take another step, the door to the house kicks open. Hiccup turns his head back to the cabin and sees four people coming out. Three of them were male and one was a female. At first sight of him, two of them drew their weapons out.

"Who are you?"one of them asked, who was apparently holding a lantern in his left arm.

"Just kill him Morgan,"said the other man who drew his weapon out. "He's just one of them O'Driscoll boys."

"Wait,wait,wait,"Hiccup stopped. "Don't shoot. I haven't introduced myself."

"We don't have time for this, Arthur,"the other man continued. "Just kill hi-"

Before he could finish, there was a sudden glowing blue just a few feet behind him. And before these strangers knew it, Toothless leaped up into the air and landed right in front of them. Snarling with pure rage and fire glowing from inside of his mouth. He roared at the strangers, who were extremely shocked about the sight of a new creature.

"What the hell is that?!" asked the third man.

"It's a devil is what it is, boss," the second man answered.

Toothless was about to attack when certain hand stopped him from doing so.

"Toothless, stop!" Hiccup demanded.

And just like that, Toothless releases his breath before he could fire and backs up behind Hiccup. Then he turns back to the man and begins to talk things through with these new strangers.

"Listen,"he starts. "We're not here for trouble. We just want to get some place warm for the night. The storm hasn't been friendly to us."

He waited for a response but there was nothing at first. Then, the third man steps forward and hands the woman over to the first man.

"Arthur, take this woman over to my horse," he said. "Micah, you check to see if there's anything else we missed in that barn. I'll talk to this dear gentleman over here."

"Whatever you say, Dutch,"said Arthur. Then Hiccup watches as he leads the woman on the back of one of the horses to their right. He turns back to this Dutch figure, who stepped forward to the pair. Toothless growled at his approach, but was again stopped by Hiccup's hand.

"What's your name boy?" asked Dutch.

"Hiccup,"he answered. "Hiccup Horrendous Haddock. And this is my friend, Toothless."

"Well, Mr. Haddock,"said Dutch. "Before I can allow you to do anything else, let me so kindly ask you exactly is your friend over here?We've never seen anything like him before."

"He's a dragon," Hiccup replied. "A Night Fury to be exact."

"A dragon? You mean like the one in fairy tale?" Dutch questioned.

"Trust me. If it was a fairy tale, I wouldn't believe it neither."

"Fair enough," Dutch said as he pulled out a lantern. "Well, if you're in need of some assistance we're so kind to help you and your friend here. Me and my friends found an abandoned mining town not far from here. You're welcome to tag along with us if that's what you want."

From there, Hiccup was surprised. To think that some stranger that he doesn't even know would invite him to his place, despite what he has alongside him. It was some generosity that the man had there. Something he had never seen before.

"Dutch, what are you doing? We can't trust them,"said the man who went by the name Micah. "We don't know if he ain't one of them O'Driscoll boys or not."

"Micah, they're out in this storm, cold and starving just like the rest of us,"said Dutch. "We don't turn anyone away. Especially in harsh weather like this. Besides, I don't think Colm would ever have a dragon lurking in his ranks."

He growled in anger by Dutch's actions. Normally he wouldn't like new people in the gang. As for Arthur, he didn't really care that much. It just meant more people for the total number of the gang.

"We should go, Dutch," Arthur suggested. "The weather's getting a lot worse."

He gave his senor gun a nod before moving to his horse. Once on its back, he looks at Hiccup, who was still waiting.

"Does your friend have some strength left?"he asked.

"Yeah,"Hiccup answered. "He's a tough one. Or at least enough to that place you mentioned."

"Good,"said Dutch. "In the meantime, take Taima for the trip back. She's a strong one too."

"Thank you Dutch."

"Like I always say. We leave no man behind."

Then, Hiccup hops on the back of the fourth horse and motioned Toothless to follow slowly. They heading back when Dutch starts talking to the woman.

"You have a name miss? he asked. At first, there was no answer. Than he tried again. "Miss?"

"Adler," she spoke softly. "Sadie Adler...Mrs...I..he...he was my husband."

"Miss, it's going to be okay," Dutch reassured. "We'll take care of you. You and the boy."

They traveled away from the burning house for a couple of miles and arrived to what seemed to be the shelter Dutch was talking about. And it was something that Hiccup was probably asking for during his time up here. There were lights all over the place. And there were at least four wooden buildings that were parallel to each other. As for the people, there weren't many. Six to eight from what he's seen. He looked back to see Toothless struggling to keep up, and saw the satisfied look on his face when he saw the view of civilization.

One of the men came out with a long weapon in his hands and pointed it at them.

"Hey, somebody's coming," he said.

He looked ready to fire, but when he took a closer look, he recognized that it was Dutch and the rest of his party and stood down.

"Looks like it's Dutch,"he said to the others. "Hey everybody, Dutch is back."

By then everyone came out of the buildings, and an old but not too old man came straight for the group.

"How'd you get on?" he asked.

Soon enough the five of them were surrounded by other people as the three men hopped off of their horses. Hiccup still stuck to Taima while Toothless stood from behind him. Eventually Hiccup moved up a bit to get a good view of everyone.

"Micah found a homestead," Dutch started. "But we weren't the first. Colm O'Driscoll and his scum beat us to it. But we found some of them there, but there is more about apparently scouting a train."

"That's the last thing we need right now, Dutch,"said the old man.

"Well, it is what it is," Dutch responded. "But we found some supplies, some blankets,a little bit of food, and these poor souls, Mrs. Adler and Mr. Haddock."

Then he brings her off of his horse and comforts her with some blankets. Hiccup climbs off of Taima and joins Dutch and Sadie's side.

"Mrs. Tilly, Mrs. Karen,"he called out. "Would you warm her up and get her something to drink?"

They moved towards the widow and lead her into the cabin. They were all about to head inside before one of the youngest women saw something from the corner of her eye and stopped.

"Dutch,"she said. "What's that?"

He turned back before remembering the dragon that they almost left behind. Luckily, Hiccup didn't forget about his best friend and motioned him to come forth. And with slight caution, Toothless moved towards the group and stopped merely a foot away from his best friend. From there, Dutch spoke.

"That's our dear friend Toothless,"he said. "Don't worry everyone. He means us no harm. I'll explain the details later."

Then the young woman nodded her head and eased herself a bit.

"Mrs. Adler, everything's gonna be okay,"said Arthur.

And before they knew it they were taken into the cabin by these gentle ladies. Leaving the men to their business.

"They turned her into a widow,"Dutch said in disgust. "Animals. I need some rest. I haven't slept in three days."

An older woman walked over to Dutch and said,

"Your cabin is over here, Miss O'Shea will show you the way."

Then she turns to Arthur.

"Arthur, your cabin is over this way."

"Thanks Miss Grimshaw,"he said as he gave her a nod.

After directing Arthur to his cabin, she turns to Micah.

"Mr. Bell, you're with the fellers over here."

Unlike Arthur in the other hand, Micah wasn't really happy with where he was sleeping.

"How come Arthur gets a room and I get a bunk bed with Bill Williamson and a bunch of "darkies?" he complained.

"Just get yourself to bed,"Arthur commented.

She ignored his complaining, she looks at Hiccup and Toothless, who were patient about where they're staying.

"And you must be Mr. Haddock,"she said.

"That's right ma'am,"he replied.

"You'll sleep with Arthur for the night. The dragon can go with the other horses, if that's okay with you."

"Okay," he said. "Normally we would sleep together, but I don't think that would be necessary due to this weather. But please, do take care of him. It's been harder on him than it has on me."

"Alright then," she said. "We'll make sure that he gets the best of care."

"Thank you,"he said politely. "Where I come from, we don't get much of people with this much kindness."

"Well, you're one of us now,"she said. "And we take good care of everyone part of this gang."

After that, she disappeared into one of the cabins, leaving Hiccup with Arthur in his went on to the cabin, in which Toothless followed. He turned back to his companion and spoke.

"Go with Mrs. Grimshaw for now bud,"he said. "She'll lead you to a bigger room than mine. Don't worry about me. It's best that we slept separately for the night. I'll see you in the morning."

Toothless nodded in compliment before following Mrs. Grimshaw into the barn just across from Arthur's cabin. She opened the door and let him in. And then followed suit and shut the door behind her.

With Hiccup, he followed Arthur into his cabin. It was a small place, but warm enough to get some shut eye for the night. He takes the bed just to the right of Arthur, who's be was at the end of the cabin. But before he doze off he wanted to say something to the old gunslinger.

"Arthur," he said as he sat down on one of the mattresses. "Thank you for what you did back there. I didn't know if I was gonna survive this night."

"It's Dutch that you should be thanking too,"Arthur said back. "But I'm glad we were able to help. It ain't easy surviving out here. Now get some shut eye. We have a busy day tomorrow."

Then, he laid down on his separate mattress, and the two drifted into sleep. Completely forgetting about what happened these last few hours.

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**So, what do you all think? There might be some updates as the chapters go by, but don't stress on it. Stay tuned for Chapter 2. Alright, Gunslinger signing out.**


	2. Chapter 2: Meeting the Gang

**Hey everyone. Welcome to chapter 2 of this entirely new crossover. Just to let you know that I might go in and out from this story. But stay clear of early chapters for these next couple of weeks. Also, expect a few updates throughout the chapter. it's only to correct any errors that might happen. As for the other stories, I might wait on them for a bit and focus on this one. Alright, enjoy the chapter.  
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Hiccup woke up that morning and thought that everything was a dream, unfortunately he realized that it was all real. He stretched his arms before collecting himself. He looked to his left and saw that Arthur still asleep on that same bed. Not wanting to wake his new acquaintance, he quietly got out of the bed and rubbed his hands.

After that, did what first came to his mind. Which is finding out where Toothless was. He came out of the cabin and went into the barn where he last saw his companion go into. Inside, he saw a number of horses that were a bit crammed in the barn. He squeezed his way through and search for his dragon inside.

"Toothless,"he called. "You in here bud?"

From what he heard, there was a little cooning noise from the platform above. Hiccup went up to the ladder and saw Toothless saying about near the window. He opens one eye and instantly pops his head up. There, he smiled his usual toothless smile and warbled at the sight of his friend.

"Hey bud,"he said. "How did you sleep?"

Toothless lets out another coon before nuzzling Hiccup's chest. There, he sat down next to the Night Fury, and allowed him to set his head on the young boy's lap.

"We finally made it,"he pointed out. "We survived the night bud. And to think that you ever doubted me."

Toothless shot a look at him before nudging him in the shoulder. He put his hands up before the dragon continued to lay on his lap.

"Okay, I'll give you that one bud,"he said. "But we were lucky to run into those guys. They saved us."

Toothless nodded in agreement to that. Only because he was right. Hiccup got up from Toothless and started heading down to the lower platform.

"I'm gonna go over to the shack just across from here. See if I can find out something about these people. You're welcome to come if you want."

Toothless nodded before dozing off to sleep. Hiccup left the barn and made his way to the shack just nearby. He rubbed his hands before opening the door to inside to , the young viking chief was met with a bunch of stares from the people inside. There was an awkward silence that filled the room. But Hiccup broke that silence with a small wave of his right hand.

"Hey everyone,"he greeted. "Care for one more person?"

"Sure,"said the old man from last night. "There's plenty of room."

Hiccup nodded before taking a seat at the chair just across from them.

"How are you holding up?" the old man asked.

"I'm fine for now,"Hiccup answered. "Just a few frostbites, but nothing too serious."

"My name's Hosea by the way,"he said politely. "Hosea Matthews."

"Nice to meet you Hosea,"Hiccup replied. "I'm Hiccup."

They shook hands for a second and then sat back down on their chairs. There they talked for a while and shared a cup of coffee here and there. Hiccup explained where he was from and what his recent past has been. And return, Hosea talked about how he and the other people were wanted men and how they were being chased up the mountains by these men that they called "Pinkertons."

"They referred to us as Outlaws,"said Hosea. "A term that was used in the west to define people like us."

"Interesting,"Hiccup replied. "And what do outlaws usually do?"

"Ah just standard things," Hosea answered. "Rob, kill... bad things that people like the Pinkertons go completely against. A few weeks ago we tried to rob a ferry just down near a town called Blackwater. It was going just fine, but then they showed up. Killed half of our people and chased us all the way up here."

"Well, I'm sorry to hear that," Hiccup pointed out. "A few months ago I lost my dad in the middle of a battle."

"Who killed him," Hosea asked in curiosity.

"My own dragon shot him,"he answered. "Was controlled by this madman and was ordered to dispose of me. But before he could make the kill, my father got in the way."

"I'm sorry to hear that too,"Hosea mourned. "Losing people is really tough. Especially the ones you love."

"That dragon is the reason why I still fight," Hiccup added. "He's everything to me. To avenge him, he challenged the dragon that ordered him to kill me to a duel. He won that duel and united all of the dragons to send it back into the seas. Now he's presumed to be the King of Dragons. Or Alpha for short."

"Speaking of that,"Hosea pointed out. "Is he...dangerous in any other way?Not to be offensive, but just out of curiosity."

"He becomes dangerous only if you startle him. But he won't harm you as long as I'm with him."

"Okay, I'm only asking this because some of us were a bit frightened to see such a magnificent creature."

"Well, he's safe to be around for now."

Several others joined them in the other seats. They were all men. One had a curve on his hat, one had a bottle on his hand and the last one had a rifle on his back. And Hosea found this as an opportunity to introduce the new guys to the other members of the gang.

"How about we introduced you to the boys, shall we?"he requested.

"Sure, why not?" Hiccup replied. "It's good to meet new people. Even if they're do-gooders or not."

Then Hosea points to the man closest to them.

"Hiccup, this here is Bill Williamson,"he said. "He used to be in the United States Army. But eventually he got stripped from his position and winded up with us."

He got out of his seat and shook hands with this new feller.

"It's a pleasure to meet you Hiccup,"he said. "I heard talk about how you fought bravely back in your home."

"Ah, it wasn't much," Hiccup replied. "I just do my best to protect my people."

Bill smiled warmly before turning back to his seat. Then, Hosea turns to the man near the cockpit with a rifle in his hand.

"This is dear old Lenny Summers,"he introduced. "His father was once beaten to death by a drunken white folk. He got his revenge eventually. Ran for his entire life. And then one day ran into us."

"Pleasure to meet you Mr. Haddock,"he greeted with a hand shake.

"Please, call me Hiccup,"he commented. "Only members outside my tribe call me Mr. Haddock."

After Lenny, he was introduced to so much more. He first was introduced to a Mexican bandit named Javier told him stories about his own country, and how he tends to do everything in his own power to avoid it. In return, Hiccup told him how he used to be the runt of his village and was avoided by everybody he knew. Including his own father.

Javier was sad to see someone who was once rejected by his own people, but was happy to hear that everything turned out to be okay afterwards. He offered him a cigarette to show his generosity, but Hiccup politely declined his offer. Saying that he doesn't smoke.

Then the door on the other side of the room opened. From there, one of the women entered the cabin with a really worried look on her sat near the fire and rubbed her hands together. Something was wrong.

"You okay there, Abigail," Hosea asked.

"It's John," she answered. "He ain't been seen in days. And the weather ain't let up. He's strong and smart. Strong at least."

Then Arthur came out from that same door. He shook off some of the snow on his coat before going straight to the fireplace.

"Hello Arthur,"she greeted.

"Abigail,"he greeted back.

He puts another log in the fireplace before he catches a worried look on Abigail's face.

"Arthur,"she said. "How you doing?"

"Just fine, Abigail," he replied. "And you?"

She paused for a second before she continued.

"I need you to...," she spoke. " I-I'm sorry, I'm sorry to ask but..."

Hiccup saw Arthur growling in annoyance and wondered what it was that he was so angry about.

"It's little John," he said. "He's gotten himself into a scrape again."

"He hasn't been seen in two... two days."

"You're John will be fine," Arthur reassured. "I mean, he might be as dumb as rocks and as dull as rusted iron, but that ain't changing because he got caught into some snow storm."

"At least take a look,"said Hosea.

Then he turns over to Mr. Escuela, who was minding his own business.

"Javier?"he called out.

"Yes?" Javier answered.

"Will you ride out with Arthur to take a look for John?" Hosea asked. "You're the two best men we've got."

"Now?"

"She's...we're..we're all,"Hosea stuttered. "We're pretty worried about him."

After finishing his cigarette, Javier got up and grabbed a Sawed-Shotgun.

"I know,"he said. "If the situation were reversed and, he'd look for me."

He handed the weapon to Arthur before heading out the door. And Arthur soon followed him after.

"Thank you,"Abigail replied.

Once they were gone, Hiccup still hung around the people in the cabin. And for each person who came in, were people that he got to meet. He talked with the women mostly. Some were Mary-Beth, Tilly, Karen and Abigail as well. From what he heard, they were astonishing things that even impressed a chief like himself. A few more minutes he still lazed about in there.

Then there was a crack from the door. They all turned to it, and next thing they knew, it slowly started opening. They waited for a second to see if it was something familiar. And before they knew it, Toothless popped his head out from the door. He continued to open it when he too was stopped by the many faces in the room.

Bill jumped out of his seat and everyone with the exceptions of Hosea, Hiccup, and Lenny panicked a little by the sight of the dragon. Toothless crouched low and growled in agitation. But was once again stopped by Hiccup.

"It's okay bud," he reassured. "Everything's cool."

Then, Toothless stood down and slowly walked to Hiccups's spot. There, he laid beside Hiccup and kept his eyes on the people around them.

"What the hell is that thing?" Bill demanded.

"Easy Bill,"Hosea calmed. "It's just the dragon from last night."

"Don't worry about Toothless,"said Hiccup. "He's usually like this when he's threatened. But inside, he's just a big softly."

Toothless shot a look at Hiccup and growled.

"No offense bud."

Then the Night Fury plopped his head on top of his forepaws and closed his eyes in contentment. He opened one eye lazily and stared at the group.

"About that,"said Lenny. "When I was a boy, my father would tell stories of dragons. But none of them looked like him."

"That's because Toothless isn't just any dragon,"said Hiccup. "He's a Night Fury."

"And what is a Night Fury, may I ask?"Lenny questioned.

"Only the one dragon that you don't want to come across,"Hiccup answered. "Back where I'm from, the Night Fury was probably the most dangerous dragons we ever had. He was nicknamed, 'The Unholy Offspring of Lightning and Death Itself."

"Really," Hosea said in curiosity. "And why is that?"

"That's just it,"Hiccup replied. "No one knows for sure. This species was so rare, they're believed to be a myth."

"But here you are sitting with one,"said Lenny.

"Yeah,"he said. "I guess that's lucky me."

"How did you two meet anyway?" Hosea asked. "It's not likely that two separate species would meet at a such accurate time."

"Well," said Hiccup. "It's a long story. But I can tell it. Since there's no other way to pass the time."

From there, he told them about how he shot down Toothless when he was just a boy, and shared about the friendship that the two formed in the cove. He also told them about keeping it all a secret from his village, and the events that followed from there. He also added his goal into uniting dragon and viking alike and the circumstances that eventually went along the way.

It was a story that took the very interest of most of the gang members. And some were most impressive about that. Others didn't mind. But fellers like Micah didn't really pay attention to such great stories from a man far away from home.

After that, he met other people as well. One such person was a little boy named Jack Marston. Who apparently was the some of both Abigail and John. He was first afraid of Toothless for what he was, but when Hiccup showed just how gentle he could be, he drew closer to return Toothless gave him a little Toothless smile that made Jack giggle a little. And Abigail smiled herself in the view of the young chief teaching her boy about his dragon.

Minutes later, Hiccup explored the mining town. Meeting other members of the gang as well. He met Susan Grimshaw the camp keeper. Who greeted him fairly. Then he met the camp cook Mr. Pearson, who told tales about how he was in the US Navy and what he did to survive out in the water. Hiccup commented that he voyaged the seas is entire life, and understood where Pearson was coming from.

Then he stumbled upon Uncle, who suffered from a disease called Lumbago. And from there he met others, including Charles Smith, Molly O'shea, Leopold Strauss, and finally Reverend Swanson. The only two that he didn't get to know better were Sadie and Micah. Sadie because he wanted to give her some space after the traumatic incident that just happened. And Micah because he left the camp before he could even say a word.

Hours later, Hiccup saw Arthur and Javier coming back with someone on the behind Javier. He seemed to be pretty injured in the face.

"Can we get some help!" Javier shouted.

"Can we get some help over here!" Arthur yelled.

Abigail came running out of the cabin with a huge smile on her face.

"You're alive!"she yelled. "Oh you're alive!"

From there, Bill and Lenny came rushing outside and ran out to Javier's horse. They lifted John carefully off and carried him from both sides of his arms. But as they carried him, he yelped out in pain.

Ah, careful idiotas!" Javier calls out. "It's his leg."

Toothless came over to see who the man was, but he didn't get a proper view. Probably because they were moving so fast. Once the three were inside, Abigail turns back to the two men.

"Thank you,"she said. "Thank you both."

Then, she followed Bill and Lenny into the cabin and came helped lay John on the mattress at the end of the room.

"This is a new low,"she says. "Even by your standards."

Once the cabin door shut, the three turned to Hosea. Who came out just as Abigail disappeared.

"Thank you," Arthur. "Thank you."

"You got any other lost maidens need saving?" Arthur asks sarcastically.

"Not today,"Hosea replied.

Then, Javier disappeared into the other shack. Toothless looks back at Hiccup, who shrugs in confusion. Then they continue to listen to Arthur and Hosea's conversation.

"Have you and Dutch talked about how we're gonna get out of this?"Arthur asked.

"I was just discussing with Herr Strauss," Hosea answered. "When the weather breaks, I suppose we'll have to keep heading East."

"East?!" Arthur bursts out. " Into all that...that civilization?"

Just hearing Arthur say that made Hiccup and Toothless wonder what he meant by that. "Civilization." What was that suppose to mean? But if it meant leaving the mountains, then it's a chance that they had to take.

"I know,"said Hosea. "The west is where our problems are worse."

Then he turns to Leopold.

"Come on, Herr Strauss. Let's get warm."

"Thank you Mr. Morgan," Strauss said to Arthur before following Hosea into the cabin.

Hiccup looked at Arthur, who started heading into his own cabin. Then he looked at Toothless. The two shared a look before following Arthur into his cabin and settling in for the night.

* * *

Three days have passed and the pair had stayed with this fine group of individuals. By then Hiccup got to know everyone. Every single soul. On the morning of the third day, he saw Arthur and Charles coming back with two deer carcasses on the backs of their horses. Much to Toothless's surprise, he had to wait before he could catch his fill.

By the afternoon,Mr. Pearson had offered them some stew. And even though that's not what they usually eat, Hiccup couldn't refuse. For he nor Toothless had eaten anything but packed up salmon that they caught a few days before. He tried it and did it taste quite good. In fact, this stew was probably better than the one that he had at home. He gave some to Toothless, who genuinely excepted it. He shivered a bit before actually getting into the taste.

And he liked it too, and they happily thanked Pearson for that. Later on, they found out that half of the gang had disappeared. Hiccup asked Hosea where they went off to, he told him that they were headed to an O'driscoll outpost just south of here.

From there, he waited for them to return. By evening, most of them came back. All except for Arthur. They waited for him to return for thirty minutes. By then,he already returned. This time, he had a person tied up to the back of his horse. He assumed that it was one of them 'O'driscoll' boys and paid no attention to it. Though he did listen to their conversation.

"Huh, said Dutch. "You found the little sh*t did you?"

"Yeah," Arthur replied. "I got him."

"Very good."

Then he drops the O'driscoll on the floor and cuts the bonds from his legs.

"Welcome to your new home," Dutch teased. "Hope you're real happy here."

"You want me to make him talk?" Arthur suggested.

"Oh no," Dutch answered. "Now all we'll get is lies."

Then he calls out a few people. It didn't take long for the other boys to come out.

"Uncle, Mr. Williamson," he called. "Tie this maggot up some place safe. We get him hungry first."

Then he stands right in front of the tied up O'driscoll.

"I got a saying, my friend," he started. "We shoot fellers as need shooting, save fellers as need saving, and feed'em as need feeding. We're gonna find out what you need."

Hiccup nodded at that saying as if it was fair. He did have a point. And to be honest, it wasn't all that bad. Next thing he knew, he heard Dutch chuckling as Bill and Dutch take the tied up feller to one of the other shacks.

"I can't believe it," he heard Dutch say. "An O'driscoll in my camp."

"I ain't an O'driscoll, mister," the new prisoner said. "I hate that feller."

"Oh, whatever you say son."

Hiccup wondered if he was an O'driscoll or not, but he knew that it wasn't his business. So he allowed them to do their work.

"Well done Arthur,"he said to his senor gun.

"I'm just sorry we missed out on Colm,"Arthur replied.

"Oh, there's time enough for that," Dutch reassured. "Now, I gotta figure out if we can hit that train."

Before he could close the cabin door, he paused. Then he turned towards the young viking and his dragon.

"Mister Haddock,"he said. "Can I have a word with you and the dragon, alone?"

"Sure," Hiccup replied. "I've got time."

He and Toothless followed the gang leader into where he was staying at and shut the door behind them. There, Hiccup took a seat with Toothless laying beside him. Dutch came out of his room and too grabbed a seat. Here, they got down to business.

"Now, as you know,"Dutch started."You've stayed with us for the past couple of days. Am I correct?"

"Yes sir," Hiccup answered.

"Good," Dutch replied. "Now, I don't know how you did it, but from those past couple of days, I've been getting visits from my people. They talked how awfully entertaining you were with you storytelling and how nice and polite you both have been. You also put yourself in a good terms with Bill 's usually a fool. Lenny takes a bit of an interest with your dragon. And Javier thinks you have a lot of empathy toward him. Now I don't usually point out people towards their successes, but I must say that I am totally impressed with how you got along so easily with the others. Even little Jack and his mom came to me just this morning,asking if you could stay with us for a longer period of time. And I'll admit, to see you with that little boy, I never seen him so happy in my life."

Then got up from his chair and stood tall.

"You bring so much joy to these people. Even after everything that happened these last couple of months. You've shown much courage and bravery. Bravery that even an outlaw like myself can't master. So, Mr. Haddock, I must ask you."

He then extended his hand out to the young chief.

"Would you like to be part of our family?"

Hiccup had to really think on that one. If he did this, then he would leave his tribe behind forever. Yet, he also thought of the circumstances that lied ahead of him. He and Toothless saw what the Pinkertons were capable of. And knew for sure that he couldn't take the chance of flying out. And from what he's seen from these people, there was no doubt that they were being hunted too.

And he's only just met these folks. And after everything they did for him and Toothless, he couldn't just reject his shot a look at Toothless, who nodded back at him. Then he stood up from his chair, stood up to the same eye level as Dutch. Then, he extended his own arm.

"Yes," he said. "Me and my dragon are most honored to be part of this gang. As long as you're leader."

"You're both are most welcome," Dutch replied. "Tomorrow, I'll make it official."

"Okay,"said Hiccup. "But before you settle in, is it okay that I make a request?"

"Sure," Dutch answered. "Anything from the likes of you."

"Put you're right hand out. Just like this."

He showed him with his right hand how it's done. His arm was out with his fingers extended.

"And why would I want to do that?" Dutch asked.

"Trust me," Hiccup said. "It'll be all worth it in the end."

Dutch hesitated at first, but eventually did as the viking requested. He put his left hand out, extended his fingers into the air. Hiccup stood to the right side and left Toothless to face the gang leader.

"Let him come to you," Hiccup instructed.

From there, Toothless slowly moved towards Dutch's hand. He was calm and gentle about it. There were no sudden movements that surrounded them. And next thing he knew, Dutch felt the scales of the dragon's head touching the palm of his hand. They were rough and smooth. More like feeling the scales of a rattlesnake. He was extremely impressed with this. Even though he didn't know what it was for. But he was about to find out from the man watching this.

"This is a symbol of trust,"Hiccup explained. "One that will carry on until your final days. For now on, you have the respect and mobility of my dragon. We owe you a debt Mr. Van der Linde. For all that you have done with will now on guide you through your journey, and fly with you until the very end."

Dutch had never heard such words from a boy such as Hiccup. And to have the respect of a prehistoric reptile, means a brand new ally for him and his gang.

"Well," he said. "I am so honored to partake in such of an action. You have guts my boy. And the gang is in need of guts."

"Just give us the call. And we'll be the first to answer it."

"Good. Now please, get some shut eye. We have a lot of work to do tomorrow."

Hiccup gave him a nod before heading outside of the cabin with Toothless following suit. Leaving an impressed to deal with some business of his own.

* * *

**So, what do y'all think. Please click on the review box to give me the details. Alright, stay tuned for chapter 3.**


	3. Chapter 3: The Train Robbery

**Here's chapter 3. I hope you're all enjoying this crossover. Because let me tell you, there is more to come. I plan n working on this whole thing daily, bu two weeks, the first half of the story should be complete. If any of you guys have any ideas, questions, thoughts, comments, or concerns pleasure type in the review box bellow. And one last thing, I still don't own anything. HTTYD belongs to Dreamworks and RDR2 belongs to Rockstar. Alright boys, enjoy!**

* * *

The next morning, Hiccup was with Toothless outside of the cabins. He was doing some tinkering with a Toothless's saddle and made a few adjustments. He saw Arthur heading into the cabin and waved a hand at him. few minutes later, he saw Dutch, Abigail and little Jack entering as well. He motioned Toothless to stay put while he investigated. He looked from the window from the cabin and saw at least Abigail, Jack and Arthur surrounding an injured feller. Which would be John from what he saw.

He tried to listen closely, but all he heard was just a bunch of gibberish. Eventually he could make out the scene just by looking at it. And nothing was good. Harsh words were being said to the injured man. And Hiccup felt a little of pity for John after all of that. Next thing he knew, Dutch came out of the cabin and started barking orders.

"Bill," he called out. "You ride ahead and set the charge at the water tower just before the tunnel."

"Ain't a problem boss,"Bill replied.

Then, Hiccup saw Hosea coming out of the cabin with a worried look in his eyes.

"Why are we doing this?"he questioned. "The weather's breaking. We could leave. I thought was lying low."

Bill then rode off to set the charges.

"What do you want from me, Hosea?" Dutch asked.

"I just don't want anymore folks to die, Dutch,"he answered.

"We're living Hosea,"Dutch shot. "We're living. Look at me. We're living, even you. But we need money. Everything we have is in Blackwater. You fancy heading back there?"

"No," Hosea shot back. "Listen Dutch, I ain't trying to undermine you. I just...I just want to stick to the plan which was to lie low, then head back out west. Now suddenly, we're about to rob another train."

"What choice have we got?" Dutch challenged.

"Leviticus Cornwall's no joke, Dutch," Hosea warned."He's-"

"Who is Leviticus Cornwall?" Arthur interrupted.

"He's a big railway magnate," Hosea answered. "Sugar dealer, oil man."

"Well how good for him,"Dutch commented. "Sounds like he has enough to share with all of us."

"Dutch-"

Before Hosea could finish, Dutch was already on the move.

"Gentlemen,"he calls out. "It is time to make something of ourselves. So get your horses ready! We have a train to rob!"

"Hey Dutch,"Arthur said as he was mounting his horse. "Why won't we take the boy with us?'

"Why would I give him a reason to?" Dutch asked.

"Because killing a man with guns is one thing,"he answered. "But if we could, intimidate them without using our guns, then that could save us some bullets. Plus, what good is a prehistoric reptile if you're not gonna use it? "

Dutch thought for a moment, but then agreed to Arthur's idea. He turns to Hiccup and calls him out.

"Hiccup," he said.

Hiccup stopped his tinkering and turned his attention to the gang leader.

"Yes, Dutch?"

"How good you at using a weapon?" Dutch asked.

"Probably as good as my dad," Hiccup replied. "Why? Do you need something?"

"Why won't you tag along with us to the railway?"Dutch requested. "Bring the dragon as well."

"Alright."

Then, he turns over to Toothless and gives him a nod. The Night Fury jumps in excitement and and allows his companion to climb up on his back. For the first time in a while, they're both given the opportunity to fly once more. And no one was happier about it then Toothless.

"Alright men," Dutch called. "We're moving out. Follow me."

And with the flicker of his reigns, Dutch finally set out. And the rest of the railway men followed them through. Hiccup gave Toothless the cue, and they both took to the skies. Hovering over the riding boys. The members that would partake this robbery were simple. Dutch was leading, with Arthur and Micah riding beside him. Lenny and Charles followed suit, and Javier covered the rear. They crossed a river and headed around a mountain. There, they followed the path into the woods.

"Okay gentlemen,"said Dutch. "Listen up. All of you."

Hiccup and Toothless had to lower themselves a little to hear what Dutch had to say.

"According to the information so kindly provided to us by Colm and the O'Driscolls,"Dutch continued. "The train will be coming down North, from Big Valley. We're gonna pick it off after it crosses the border into the Grizzlies. There's a raise spot that should give us a good advantage."

They continued through the forest and passed a frozen lake.

"Charles, you'll keep lookout for any outriders. How's that hand by the way?"

"I'll be fine,"said Charles.

"Good," Dutch replied. "I'll take the driver and engineer, then run point. Lenny and Javier, you take the front cars and deal with any guards. Arthur, Micah, and Hiccup, you head straight for the back. Have your dragon sniff out anything we miss."

"Why's that?" Hiccup asked.

"That's what we're after, son," Dutch answered. "Mr. Cornwall's private car."

"You and me Morgan,"said Micah.

"Great," Arthur said in disgust.

"Have you got a problem with that?"

"Not if you keep your head for once."

"You worry about your self, huh?"

"ENOUGH," Dutch stopped. "After Bill blows the tracks, we're gonna need to move fast. Is everyone clear on what they're doing?"

"Yes, sir,"said Hiccup.

"Yeah,"Arthur answered.

"Crystal,"Micah replied.

"Yes boss,"Lenny points out.

"Good,"Dutch replied to all. "Now come on, let's ride."

They traveled around the mountain and down into a pass. They were headed down the mountain. Trees started to thaw up. And grass started to appear in the ground bellow. For once Hiccup as something that wasn't snow. He touched Toothless by the side of his chin and then pressed on.

"Out of snow finally," said Arthur.

"I haven't seen this type of weather for days," Hiccup pointed out. "It's good to be finally out of that nightmare."

"Well we need to get this done fast now that it's thawing,"said Dutch. "Before anyone gets up here after us."

Dutch then turned back and looked at his comrades with great dignity.

"Ah, look at you boys,"he shot. "See, this is what I call a crew. Micah Bell, Charles Smith, Arthur Morgan, Javier Escuela, and what about young Lenny here, always the first man on his horse. And let's not forget about dear Hiccup here, and his eyes in the skies."

"Just happy we're out of that weather Dutch,"said Hiccup.

"Are you sure you're ready for this, kid?" Javier questioned.

"Of course I'm ready," Hiccup answered. "This isn't the first time I did something like this."

"Now stay calm," Dutch reassured. "Keep your eyes sharp. That goes for all of you. No mistakes. Not again."

"So we do this," said Micah. " Then we go back to Blackwater and collect."

"How many times you gonna ask the same question, Micah?" Arthur asked.

"That's a lot damn money to leave sitting for too long," Micah answered.

"It would be crazy to go back there now," Charles shot. "The place will be swarming with Pinkertons."

"What's in Blackwater that your so dying to get back Micah?" Hiccup questioned. "I'm sure you'll have plenty of time to collect it."

"Nothing that needs to concern you lizard-boy," Micah answered harshly.

Toothless growled at his words, but was reassured by Hiccup that he meant no offense.

"We go back when I say we go back," said Dutch. "And that's the end of it. The money's safe. You'll just have to trust me. And if Colm is right, there'll be a stack of railroad bonds on the train. Good money. Once we work out how to cash them. Now everyone, shut up and get your mind on the job at hand. Come on."

They continued down the mountain and stopped at a ridge just on the side of a tunnel. There, Toothless landed right in between Dutch and Micah, and looked ahead. On the side of the railroad tracks, they saw Bill working on something.

"Arthur," Dutch called out. "You wanna go down there and see how Bill's going on?"

"Okay,"he answered.

Then, he guided his horse down the ridge and rode straight to Bill. The others waited for his in the meantime, Hiccup had a little opportunity to strike up a conversation.

"So, I never had a chance to ask, Dutch,"he said. "What exactly is this train we're gonna rob?"

"Well as far as I'm concerned Hiccup," Dutch answered. "This train will be filled with cash. Enough for us to get off this mountain. Why? You ever robbed a train before?"

"Well, when you put it like that,"said Hiccup. "Me and Toothless have been with you guys for only a few days."

"Well, I suppose it wouldn't hurt to give you a little information. Trains are the next stage of transportation of this country. The government likes to keep building new technology in the US. And most trains carry a lot of money. Money like us outlaws need. This train has a stash of railroad bonds hidden somewhere in the back. And those bonds are worth a lot of money. And we need that if we're ever gonna get off this mountain. Does that answer your question?"

"Yeah,"Hiccup replied. "I already know how money works so I won't ask you that."

"Good,"said Dutch. "I need you to stay strong for this score. We'll need all the help from your friend here. How is he by the way?"

"He's good for now. Like you said before, we all know what to do. And Toothless is strong and ready to tackle this mission. Right bud?"

Toothless warbled before looking down at the scene once more. He saw Arthur coming back up the ridge and regrouping with the rest of the gang. He seemed to be in a good mood which was a good sign.

"Everything okay?" Dutch asked.

"I guess so," Arthur answered.

"Alright, cover your faces," Dutch ordered. "The train should be here any minute now."

Next thing they knew, everyone was covering their faces with clothe-like masks. Hiccup didn't really have a mask, so he just used his helmet. Which didn't go unnoticed by young Lenny.

"What's with the helmet?" he asked.

"Oh, it's just something that I carry around with me," Hiccup answered. "Unlike you guys, I don't have masks that look just like yours. And Dutch said to cover our faces and I just thought that I'd cover mine with something of my own."

"Fair enough," said Lenny.

They waited for a couple more minutes before it finally arrived. The train was coming straight for the tunnel, and the trap was set. It was only a matter of time for the crew to do last minute preparations.

"Gentlemen, it's time," said Dutch. "Now good luck. All of you. You all know what to do."

From a distance, Bill hid near the rocks and placed his hands on the detonator. He waited for the right moment before blowing the charges. But for some reason, it didn't go off. He tried it a couple of times. but it still didn't go off. Something wasn't right.

"Oh," Dutch complained. "You've got to be kidding me!"

"Where did you find that moron?!" Arthur questioned.

"You said it was fine!" Dutch shot.

"So it's my fault."

"Come on!" Javier shouted.

Then he, Lenny and Arthur dismounted their horses and ran straight for the other side of the tunnel.

"You're pathetic," Arthur said before following them. "You know that?"

Dutch looked down in frustration and turned to the remaining people.

"Micah, Charles. you're with me," he said. "Hiccup, you and your dragon make sure those boys stop that train."

With a nod, Hiccup turns to his dragon.

"Let's go Toothless."

Toothless lets out a small growl before turning back and followed the other three. Toothless galloped down towards the other side of the ridge. He already saw the three jump, and hoped they were okay. Once they reached the edge, Toothless jumped down and extended his wings. And with the ground not to far down,he pulled up and started soaring though the air. Flying as the train moved fast.

Hiccup looked up and saw that Arthur and Lenny made it. But noticed that Javier slipped off the train and was left behind. He turns to Toothless and insists that they helped him. And with a nod, the two swooped down towards the direction of their fallen comrade.

"Javier," he shouted.

The Mexican outlaw looked back and saw Hiccup and Toothless flying straight at him. Then he starts running towards them. He was expecting them to land, but what he didn't realize that Toothless extended his paws out. He stopped dead in his tracks before his felt himself being quickly lifted off the ground.

They ascended up into the sky, but still stayed in range of the caboose part of the train. Javier admitted to himself that this was his first experience flying, but he recollected himself and regained his self confidence. All he had to do was not look down.

"Don't drop me now,"he said to Hiccup.

"We got you Javier," Hiccup responded. "Climb up."

He extended his arm at Javier, and pulled him up to the saddle. There, he placed him behind him and continued to fly towards the train. They looked on as it passed a bridge, and saw Arthur saving Lenny from sudden death.

"Take us alongside the train,"Javier commanded.

Toothless flew just to the right of the train, and moved close enough for Javier to jump down. With one leap, he stuck his landing on top of one of the train carts and regrouped with the two others.

"We need to stop this train,"Arthur said to Hiccup. "Fly ahead to the driver section. Get him to put on the brakes."

"Okay," Hiccup respond. "Come on bud, let's stop this train."

With one burst in the air, Toothless sped up. Looping and turning to the left side of the railway and flew towards the front of the train. He spotted the driver working some mechanical machinery in the front of the train. Hiccup noted it's mobility, and mentally took notes. But then focused on the task at hand.

"Alright Toothless,"he commanded. "Show'em what you got bud."

With a growl, Toothless shot out a plasma blast that hit the side of the train. The explosion put the driver in shock, he took cover at the front and pulled out a gun.

"Be careful, bud,"he warned. "We don't want to have another incident like the last one."

Toothless then became extremely careful. The driver pointed his gun out and started shooting at the dynamic duo. Toothless dodged one bullet and avoided another. He was fast, but it wasn't gonna last long.

"Try to move in front of the train, Toothless," he said. "He won't have a good shot from there."

Then he sped up once again, but instead of flying above the train, he flew just beneath it. Avoiding shots from being fired. When they were close to the edge of the front of the train, he saw Arthur, Lenny and Javier catching up. But it didn't change a thing. He and Toothless still flew ahead of the train. He looks back to see from the corner of his eye, the driver hiding behind a pile of rocks with a shovel in his grasp.

Then, he saw the driver hitting Arthur with that shovel and strangling him with his bare hands. This angered Hiccup a little, and he encouraged Toothless to go faster. When they were much of a great distance from the train, they made a sharp U turn and flew straight at it with full speed.

They watched as the struggle continued. Arthur put the driver in a good spot before the pair ascended a little. Once in range, Hiccup orders Toothless to fire. He releases another plasma blast which hits the driver's back. Creating a small explosion. The impact forced the two back. Arthur fell on the floor of the train cart, and the driver rolled off the train and into the grass just to the right side.

It took Arthur a minute to recover, but he regained himself and went inside the front cart. He pulled some lever and puts on the brakes. And slowly but surely, the train started to stop. It halted just in the middle of the forest not far. There, Hiccup watched as Arthur exits the train cart and takes cover near the bushes.

Then he saw a bunch of guards coming out of the train and starts shooting at the three. They fought well, but they were still outnumbered. They had to help them. So with a swift loop, they dove down to the scene. Once close enough, Toothless fired a plasma blast at a group of guards just in front of the trio. They came back for another run before they started getting shot at themselves.

They did their best to dodge the incoming bullets. But Hiccup knew that they had to think of another plan. Then suddenly, he thought of one.

"Get us closer bud,"he told his best friend. "I got an idea."

With a nod, Toothless dove down closer to the guards. Dodging every single bullet they tried hitting them with.

"Hold, Toothless," he said ad he activated Toothless's prosthetic tail. He waited a little bit before giving him the cue. "NOW!"

He pulls a lever from Toothless's side and lowered themselves. The guards bellow looked to their left and the duo closing in on them. They turned their guns to them and were about to fire, but they were too fast for the army bellow. Once they passed them, Toothless flew up and pulled up to the sky,where he flew upside down. The guards kept a close watch on the eye in the sky and were shocked to see the rider that was on the back of the dragon missing. They looked around to see the young boy gliding straight at them. He was wearing some kind of wing suit with actual wings sticking out.

The person in front aims his rifle at him, but before could pull the trigger, he was kicked in the face by this new comer and was forced to the ground. There, Hiccup found himself surrounded by the other guards. Who too have their guns pointed at him. But that's what the viking chief wanted. He pulled out some strange device from what the other boys could see. And before they knew it, a long blade extended from that device and was glowing with fire.

That's when the fighting starts. They start firing their guns at him, but he reflects the bullets with his sword and presses on. He counter attacks a coming guard with his sword and pushes him away. Then the next guard attacks him from his front left. But the young viking sees him coming and blocks his attack. Then, while off guard, he kicks him off balance and lends a blow straight to the head. Knocking the guard out cold.

Then he clashes with two other guards to his front sides. Pushing them back with his swords. He flings the wrist of his right hand, and shoots out darts from that wrist at the guards. The darts hit three of them, and they fell to the grass bellow. Then he decided to press on once more, dealing with more guards as he kept going. After dealing with five other guards in the other hand, he found himself in a tight position with one of the toughest guards. Who had him pinned against a rock.

"Any last words, outlaw scum," said the guard.

Hiccup worried a little bit, but when he saw a shadowy figure just on top of the train cart above the guard, he smirked.

"Yeah,"he said. "Could you kindly step out of the way? I'm trying to get a good view of my friend here."

The guard then turned back, and saw the dark form of the Night Fury. Who glowed a light blue in the night. The Alpha Dragon raised his head high, and shot a plasma blast at the guard. Blowing up his head clean off. Then, he jumps down from the cart and helped his companion up.

"You know I had that one bud," he said.

Toothless gave him another look before turning his attention to the other guards. He snarled at their presence and was amped up for a fight.

"So," said Hiccup. "Shall we?"

Then, the two charged at the army of guards. Dealing with them as they went on. Hiccup bashed on guard in the head, and Toothless rammed him towards a tree. Then Hiccup holds one guard by his knees, and Toothless swings his tail at him as if he was a baseball at the other guards. And although they had their fun together, it didn't go unnoticed by the others. It drove the likes of Javier and Lenny. But Arthur, he saw something in them that could highly bring success to the gang in the future. But it was best that he saved that for after the robbery.

So the five of them pressed on, fighting their way to the back of the train. Unfortunately for them, there was too many of them. They couldn't fight them all. They soon found themselves being pushed back. But that wasn't for long, because the rest of the crew showed up minutes later. Riding from the North and cutting down the number of guards. They kept fighting until there was only one last man left. In which Hiccup shot in the back with a dart as he was high tailing.

"I can see why the O'driscolls brought so many boys up here for this," Lenny commented.

"You four alright?" asked Dutch.

"Yes," Arthur responded. "Let's get the money and go."

"Dutch," Micah called out. "It seems that we've got some fellers hold up in this last car."

"Awe sh*t," said Arthur.

"What are you boys planning in there?" asked Bill.

Dutch stood outside of the train car with the other crew members lined up behind him. The train door seemed to be sealed shut from the inside. Which made things a bit complicated. But Dutch had a way of dealing with complicated situations.

"Listen to me," Dutch started. "We don't want to kill any of ya. Anymore of ya anyway. I'd give you my word but trust me, we will!"

"I work for Leviticus Cornwall," one of the guards said. "We've got our orders."

"Alright, you asked for it," Dutch said as he held up his right hand. "Five...four...three, two, one."

Then there was no reply. Guess that meant that they had to do things the hard way. Now Hiccup would be a more empathetic guy when it comes to things like this. But if he and Toothless were gonna survive this, then they had to deal with this differently. And they needed that money. So they had no other choice. Dutch turned back to his crew mates, who were waiting his command.

"Gentlemen,"he said. " It seems that our friends have gone deaf. Wake'em up a little!"

Then, Hiccup saw as the gang members pull out their weapons and started firing at the front of that door. They fired their guns for more than ten seconds. And yet the people inside still wouldn't open it.

"That's enough!" Dutch commanded. "Mr. Williamson, give Mr. Morgan and Mr. Smith some dynamite. You two boys go blow that door open."

Before he could though, Hiccup stopped them.

"Allow us to, Mr. Dutch," he suggested. "Toothless can be a great shot when it comes to opening doors. Right bud?"

Toothless warbled a little bit before moving up.

"Very well," Dutch granted. "Go ahead and do your thing."

The other members took a step back and let the young chief and his Night Fury get into firing range.

"Now it don't matter too much to us," Dutch advised. "But you boys in there, you might wanna take a step. back."

Then Toothless was all that was left who was standing right in front of the door. He looked back at Hiccup, who nodded his head and gave him the signal. then, with a deep breath,Toothless fired a plasma blast at the door. When the dust cleared in the other hand, the door still wasn't open. He popped his head out and looked back at the other members, who weren't really impressed.

He turned back and tried it again, firing another plasma blast at the door. But once again, he was up to no success. He looked back again and saw the other members still unimpressed. He dropped his head down and made a low, groaning sound in shame. Then, he looked to his right and saw the other horses who were lurking about. Not really paying attention to the scene.

Then he saw Dutch's horse, The Count, popping his head up and looking right at him. He stared for a second before dropping his head down and grazing in the grass down bellow. That was when Toothless thought of something. He turned back to the cart with a thinking look on his face. Then he closed his eyes. Preparing to unleash his fury. Before the gang members knew it, they saw Toothless spitting the spines on his back and were surprised to see his back glowing blue.

Toothless slowly rose up on his hind legs and extended his wings. He started to glow from everywhere. He bared his teeth, and he narrowed his eyes. And with a fierce roar of thunder, he released the most powerful plasma blast he could think of. The impact of the blast sent a shockwave from miles around. Next thing he knew, the gang members were taken back a yard and the horses began to panic.

It was only a few seconds before they all started recovering from the blast. Micah, Bill, Javier and Lenny coughed from all of the smoke, while Dutch and Arthur were completely shocked by the found Hiccup leading against a tree. Waiting for them to regain themselves.

"How did you know that it was going to be powerful, Hiccup?" Dutch asked.

"I don't know," he answered. "I guess I'm so use to Toothless's plasma blasts that I can't tell what's powerful to him."

"Well," said Arthur. "Let's hope it was enough to blow the door open."

They turned back to the door and saw that it had a huge hole in the middle. The sides looked burnt up, and the doors were half torn. Fortunately for the men inside, they were all alive in well.

"Great job bud," Hiccup congratulated.

He patted Toothless's right shoulder. And in return, Toothless looked back with a smile on his face. But before he could get comfortable, he turns his attention to the workers and growls. The other gang members pulled out their guns and pointed them and the individuals guarding the cart.

"Alright, come on," said Dutch. "Just walk on out here. We don't want to kill you folks. We just want to rob your boss."

Then one by one, the workers came out. There were three of them to be exact. Once they were off, Bill and Javier guided them over to the rocks nearby. Toothless kept a close eye on them as they were guided out of the train. And then turned back to Dutch and the others.

"Arthur, Lenny, Hiccup and Micah, get on up there," Dutch ordered. "Search that train. Take the dragon in as well."

Then the five of them entered the train, and was it something that Hiccup wasn't expecting. Inside the cart, everything was astonishing to the young boy. There were leather seats that stood in the ends of the cart. Great fabrics covered all of the windows, and did it all look solid gold. It was nothing that Hiccup has ever seen in his entire life.

"Wow,"he said in amazement. "What is this?"

"Look at this place,"said Lenny. "It's like a palace."

"Now I've seen everything," Arthur commented. "Micah, Lenny, you take the safe. Hiccup, you and me search the rest. Find anything that could be valuable."

"You got it Arthur," said Hiccup. "Alright bud, find something that could be in good use to us."

Then, they scattered all over the place. Looking for any valuables. Hiccup searched the cabinets to the right while Arthur searched the drawers to the left. Hiccup found a few letters as well as a watch. And Arthur found a few bucks, plus a bottle of brandy sitting on one of the tables. Toothless started sniffing about and found something in one of the drawers on a table just at the center of the cart.

"You got something bud?"asked Hiccup.

Much to Toothless's curiosity, it was a bit difficult for him to open the drawer up. There, he found a lot bill stacks just sitting in there. And from what Dutch told him, it was money. He took it all and stashed it in his satchel that he carried inside. Then he and Toothless kept searching. It was a few more minutes before Micah and Lenny opened up the safe.

They found only a few things. Mostly contracts from Cornwall's sugar deals from the west side of the middle of nowhere. It wasn't all that interesting. He turns to Arthur, who was already at the back of the cart searching.

"You got anything?"he asked.

"Not much," Arthur answered. "But still something worth searching."

"Keep looking," Micah insists. "We need to be sure we got everything."

Toothless kept sniffing until he yet again got another scent. He went over to the right side of the back of the cart and started clawing into a cabin. Then Hiccup steps in and searches the cabin. When he got to the bottom drawer, he found something very interesting. There were a few papers, they looked like money, but they really weren't.

"I got something," he said to the other boys.

Arthur goes to his position and takes a look at what he found. Hiccup hands him the papers and asks if they were a sign of money. But Arthur had this interested look on his face. And turns back to Hiccup.

"These, are bonds Hiccup," he said. "Their usually worth a lot of money, but we'll get more info from Dutch. But in the meantime, good work."

Then, he started heading out of the cart with the duo following suit. They came out of the cart, where they regrouped with the rest of the members.

"So,"said Dutch. "What did you find?"

"These," answered Arthur. He handed him the papers where Dutch so kindly examined them. "They're worth anything."

"Oh, sure," Dutch answered. "Bearer bonds. I think we can probably sell these pretty easily. Well done."

"Oh, it wasn't me who found them," Arthur admitted. "The boy and his dragon found them first."

Then Dutch turns over to the duo with a really impressed look on his face.

"Good work gentlemen," he said. "You've done pretty well."

"Ah, I think the credit goes to Toothless over here," Hiccup pointed out. "He was the one who sniffed them out."

Toothless walked closer to Dutch, who was received a rub on the top of his head by the gang leader.

"That's some creature you have here Mr. Haddock,"he complimented. "If we had a few more like him, then robberies these days would be a lot easier. Great work."

"Oh, and another thing, Dutch," Hiccup said as he pulled out something from his satchel "I found a few of these bill stacks stashed up in the cabinets. It's yours if you want it."

"Oh, you can keep that," Dutch insisted. "You've earned it today. Both of you."

Then he dismisses the dragon and looks back at the workers. He turns his attention to hi trusted senor gun, who was awaiting his orders.

"Arthur," he calls out. "Would you get rid of all of this?"

"And the train?" Arthur questioned.

"Yeah," Dutch responded. "Get it out of here."

"And what about them?"

"What do you think?"

"I don't know."

"It's up to you. Kill'em, leave'em here, take'em with you on the train. Just make sure they don't send no folk after us."

"Okay."

Then, he and the other members mounted up on their horses. Hiccup did the same with Toothless.

"Oh, and Arthur," said Dutch. "When you get back. We'll be moving on. The rest of you, let's ride!"

Then, with the flicker of the reigns of his horse, Dutch and the rest of them were on their way. Leaving Arthur to clean up the mess they made. And headed back to make preparations to finally get off this living nightmare.

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**What do y'all think. Impressed? Please click on the review box bellow. Alright, stay tuned for chapter 4.**


	4. Chapter 4: Moving to a new camp

**Hey everyone. Here's chapter 4. I just want to take a moment to thank all of you who are following my story. Because out of all of my stories, this one is the best one yet. Oh, and in that last chapter I forget to mention. There is a "Hidden World" reference that I put in there. If anyone finds it out has discovered a great mystery. I also might throw in a few things of my own in the mere future. Alright guys, enjoy. **

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When they returned to camp, Dutch called out to everyone else and told them to start packing. Hiccup and Toothless helped along. Moving boxes and containers onto the back of the wagons. And even though they were doing their part in helping, they both took note that there has been some strange behavior within the lady half of the gang. Mrs. Grimshaw turned into once a nice and polite old woman, into a strict and overbearing arbiter. And they both quietly told themselves to not go on her bad side. She kept barking orders at the rest of the women, telling Mary-Beth to stop reading and go help, telling Tilly to work faster, and scolding Karen for not trying as hard. In which Hiccup felt bad for.

There were five wagons in total. From which they had to load as many containers as they could. Which was an easy task. Hiccup took the smaller ones and Toothless took the bigger ones. And for each wagon, meant at least six to seven different things. They also loaded a bunch of sacks onto them as well. Which was probably the easiest of tasks. They kept loading for half an hour before Arthur finally returned. He dismounted his horse and met up with the caravan.

"So, we finally getting out of this hellhole?"he asked.

"We're gonna try,"Dutch answered. "The weather seems stable."

"And we just robbed a Leviticus Cornwall train," Hosea added.

"We got money in our pockets," Dutch shot. "The worst is behind us, gentlemen. So the question is, where now?"

"I know this country a little," Hosea responded. "I told you. We should set up camp in 'Horse Overlook' near Valentine. We'll be able to hide out there no problem, as long we keep our noses clean."

"Well then, let's go," said Dutch. Clean noses and everything else."

Hiccup and Toothless had finished loading the rest of the supplies when he saw everyone mounting the wagons. They also saw Lenny and Bill loading John onto the back of the second wagon.

"Arthur," said Dutch. "You're in that one. Bring Hosea along too. I know you two like to talk about the good old days and 'what's gone wrong with good old Dutch."

Dutch mounted up the first wagon when he saw the young pair waiting orders.

"Mr. Haddock," he said. " You ride with Arthur and Hosea. Stash that dragon of yours in the back so that no one sees him."

With a nod, Hiccup and Toothless went over to the back of the caravan. Hiccup climbed up the front of the carriage and sat next to Arthur,Hosea, and Charles. While Toothless walked to the back of the wagon and climbed in. Hiccup looks back to see Toothless giving him with curious yet inquisitive look. Hiccup reassures him with a hand to the side of his chin.

"It's okay bud," he said. "We're finally getting out of this nightmare. But we have to be vigilant. We don't know what's down there. So, please don't draw any attention."

Toothless nodded in agreement before he circled up and laid down in the back of the wagon. It was only a matter of seconds before they were on their way. Finally moving from the old mining town to the new camp in the woods bellow. The journey was long, but worth the wait. They traveled for countless miles, passing a frozen lake just not far. By the time it reached noon, they were already coming down a hill and into the trees. Some of which, Hiccup admired. He looked back to see Toothless taking a nap. And he quietly covers him with a blanket.

It was over another hour before he saw Lenny and Micah moving closer to the front wagon. He didn't hear much. But before he could investigate, he saw them two riding ahead and leaving the caravan behind. He wondered what Dutch ordered them to do, but didn't really pay attention to it. He was just glad to be finally off that mountain. They traveled for another hour before crossing a river that was just near a waterfall. They crossed the river before they ran into big one of the wheels broke off, and everything started falling apart. All of that noise woke Toothless up and growl in suspicion.

"Aw, sh*t," Arthur cursed as he looked back at the mess.

"Okay,"said Hosea as he hopped off his seat.

They hopped down from the carriage stood where the wheel was suppose to be. Looking down in suspicion and frustration. The wagon in front of them stopped and next thing they knew, Uncle and Javier were looking back at them.

"You alright back there?" asked Uncle.

"Does everything look alright?" Arthur responded sarcastically.

"Well, what's going on?" Javier questioned.

"Aaaaaagh, I broke the g*dd*mn wheel," Arthur answered in frustration.

"Alright, let's get it fixed, " said Hosea.

"You need help," asked Javier.

"I reckon we can handle it," Hosea replied.

Then, Arthur moved towards the wheel and started picking it up. Hosea and Charles positioned themselves at the two rear ends of the wagon so that they could lifted up for Arthur to place the wheel back. Hiccup was the last to climb down and offered his assistance.

"You need any help with that?" he asked.

"Sure," Hosea acknowledge. "Just help us lift the side of this wagon so that Arthur can put the wheel back on."

"Okay."

Then the young viking chief turns to his dragon.

"Toothless," he said. "Go in the middle of Hosea and Charles and help them lift it up. I'll go round up the stuff that dropped."

With a nod, Toothless lifted the carriage up using his head as leverage. As he, Hosea and Charles lifted it up, Arthur rolled the wheel onto the wagon.

"You still strong enough to hold up a wagon, Hosea?" Arthur questioned.

"Shut up!" Hosea responded.

"I'm just saying," Arthur shot.

"Well, say less," Hosea countered.

Once he was close, Arthur placed the wheel to its previous spot and started bashing it in. Hosea and Charles admitted to themselves that it was pretty uncomfortable to be right next to a they didn't mind. But apparently, they were pretty impressed with the Night Fury's strength. They could barely lift it themselves. It took Arthur only a few tries before the wheel was fixed. Once it was all tinkered up, Hiccup just finished rounding up all of the items that fell out.

"See," Arthur said to the King of Dragons. "You ain't so useless, after all."

Toothless shot him a look before rolling his eyes. But before he could climb up the back, he saw something just up the hill behind them. He crouched low and growled, which caught the attention of Hiccup.

"What's wrong bud?" he asked.

Then, when he looked at what his companion was looking at, he saw it too. There were three strange men that were on horses. It didn't take long for the other guys to spot them too.

"What do you think?" Arthur asked Charles.

"If they wanted trouble," he answered. "We wouldn't have seen them."

Hosea gave them a small wave before they disappeared into the forest.

"Poor bastards," he said. "We really screwed them over down here. Come on. Let's not push our luck."

"What happened?" asked Arthur.

"Get in," Hosea answered. "And I'll tell you."

Then, they all walked towards the seats and hopped on the back of the wagon again. It was only a matter of seconds before they were on the road climbed up the back and moved closer to the seats to listen. It was at that moment when Hosea began to explain to the curious boys. With the exception of Charles.

"So, yes," he started. "The Indians in these part got sold a very raw deal. This is the Heartlands we're going to. Good farming and grazing country, they lost it all. Stolen clean away from them it was, every blade of grass. Either killed or herded up to the reservations in the middle of nowhere."

"And how is that different from anywhere else?" Charles questioned.

"Well, maybe it's not," Hosea responded. "I just heard some of the army out here was particularly, uh, unpleasant about it."

"Unpleasant?" Charles shot. " How do you rob and kill people pleasantly?"

"We don't," Arthur replied. "In spite of Dutch's talk."

"I fear I was perhaps trying to simplify something more complicated for the benefit of our block headed driver here," said Hosea.

Hiccup and Toothless tried to hold back their laughter, in which Arthur failed to notice.

"Hey," Arthur countered. "Don't blame it all on me. Never forget, this here's a conman, boys. Born and bred at the same time. Just cause it sounds fancy don't mean he knows a damn thing about what he's talking about."

They rode for a couple more miles before something hit Hiccup.

"Hey, Charles," he said. "I never got a chance to ask this. What happened to your tribe? You told me back at the other camp that you were a part of one."

"I don't even know if I have one," he explained. "At least, not that I can remember. My father was a colored man. He told me he lived with our people for a while. A number of free men did. But, when we were forced to move from our lands, the three of us left. I was too young to really remember much. All of my life I've been on the run. A couple years later a number of soldiers captured my mother and took her somewhere. We never saw her again. Me and my father drifted around a few times. He was a very sad man and the drink had a mean hold in him. Around thirteen, I was took off on my own."

"Huh," said Hiccup. " I remember something like that too. Back where I'm from, my father took a mean term to dragons. He had a really bad hatred to them and swore to slay every last one of them. But he wasn't always like this. When I was around two years old, all he knew about was to protect his people. No matter what the cost. But when my mother was taken by dragons, it broke his heart. Next thing you know, he had so many maps around the house. Trying to find nests and home bases for all dragons alike. But when I met Toothless when I was fifteen, it all changed. Now, he had a forgiving side to dragons. He even had one of his own. When I was twenty, after so long, he finally found my mother. The two reunited after I found her hidden in some caves in the middle of nowhere. I never saw him so happy before. \When I was twenty-one, I was given his position of chief after he passed away. And that's a young age for being chief."

"That was about the age we found young Arthur here," said Hosea. "Maybe a little older. A wilder delinquent you never did see. But he learned fast."

"Not as fast as Marston, apparently," Arthur stated.

"Wait, I don't understand,"said Charles. "What's the problem between you two?"

"Yeah," Hiccup added. " You never told us back at camp up there. Did something happen that made you two like this?"

"Arthur," Hosea pointed out.

"It's a long story," Arthur answered. "I'll tell y'all another time. But let's just get to camp first. And speaking of that,we still heading in the right way?"

"That depends," Hosea responded. "Are we still heading west in search of fortune and repose in virgin forests as we planned? No. Are we heading in the correct direction on our desperate escape from the law eastwards down the mountains? Yes, I believe so."

"You know this area?" asked Hiccup.

"A little," Hosea answered. " I've been through it a couple times. There's a livestock town not too far from here, called Valentine. Cowboys, outlaws, working girls. Our kind of place."

"O'Driscolls?" Arthur questioned.

"Probably them too," Hosea replied.

"Pinkertons?!"

"Let's hope not."

"And this place we're going to, wait, what was it called again?"

"Horseshoe Overlook," Hosea points out.

"It's a good place to lie low?"Arthur asked.

"It'll do for now," Hosea answered. "And how low do you think Dutch is gonna lie? It's just...you know, maybe it's me who's changed and not him. But, we kept telling him that ferry job didn't feel right. And remember, you and me had a real lead in Blackwater that could've worked out."

"Maybe," Arthur shrugged.

"It's just," Hosea continued. "It isn't like Dutch to lose his head like that."

"Things go wrong sometimes,"Arthur stated. "People die. It's the way it is. Always has been. Me, you, Dutch. We've all been in this line of work for a long time. And we're still here so, I figure we must've got it right a hell of a lot more than we got it wrong."

The rest of the journey to the new camp went calmly and was quiet. Everyone remained silent and decided to do their own things to past the time. Arthur kept riding, Hosea was working on something with a bunch of herbs, Charles was busy sharpening his knife. And Hiccup looked back and tended to his dragon. Feeding him a fish that they caught while up in the mountains. They continued to ride up until they reached an area surrounded by trees.

There, they met up with Javier, who was waiting for their arrival. He climbed up the back , being as careful as he could to not wake the sleeping dragon, and accompanied them through the rest of the traveled for another few minutes before finally reaching their destination. Once they were st the sight of camp, Hiccup turned around and started waking Toothless.

"Hey, good morning bud," he said.

Slowly, Toothless started to open his eyes. He looked at his surroundings and saw a whole bunch of new. He popped his head up, and started sniffing at the new scent of fresh air.

"That's right bud," said Hiccup. "We're here."

Toothless climbed down the wagon and started exploring their new temporary home. He looked around and saw people getting to work. He saw Bill, Javier, and Uncle tethering the horses to a few hitching posts and watched as they removed the saddles and carriage gear off them. Then, he saw Karen, Mary-Beth, and Tilly setting up the tents from the wagons. And the last thing he saw was Pearson and Grimshaw preparing thing that had to deal with supplies. It was all new fresh smells that had Toothless curious. And he couldn't wait to get started.

But much to Toothless's surprise, he saw Hiccup walking with Arthur and Hosea, who were meeting up with Dutch. He slowly followed his companion to listen to more of the conversation.

"You weren't wrong, Hosea," said Dutch. "This place is perfect."

"I hope so," Hosea replied.

"Gentlemen," Dutch said in accomplishment. "We have survived."

"For now."

"Now, it is time to prosper."

"Arthur and I were about to prosper in Blackwater," Hosea pointed out. "We were onto something big. Then, Micah got you all excited about that ferry, and here we are."

"We have all made mistakes over the years, Hosea," Dutch replied. "Every last one of us. But I kept us together, kept us alive. Kept the nooses off our neck."

Then Dutch started walking toward the center of camp. With Hosea, Arthur and Hiccup tagging along.

"I guess I'm just worried,"said Hosea. "I ain't got that long, Dutch. I want folks safe before we go."

"Me too."

"And now here we are. East of the Grizzlies, and out of money. And a long way from our dream of virgin land in the west."

"I know, my brother," Dutch shot. "But we are safe. We make a bit of money here, then we move again. Head out around them, be west of Uncle Sam,and in few months buy some land."

"I hope so," Hosea replied.

For a moment, Dutch chuckles before walking backwards a little bit. Then, he started heading towards the cliff and looks at the view.

"Would you just look around you," he said to Hosea. "This world has its consolations."

Hiccup and Toothless looked at each other and wondered what he meant. But didn't really give into the situations. Then, they saw Leopold coming about from behind.

"Gentlemen," he said. " I am going to head into the local town and, you know. See if I can strike up a little business."

"Of course, Herr Strauss,"said Dutch. After he was gone, Dutch turns back to the other four. "I prefer robbing banks to usury. Seems more dignified somehow."

The other four nodded in understanding. After that, Dutch calls to the others.

"Everyone," he said. "Put your tools down for a moment. Come on, gather around. Quickly now."

They all gathered around to what was to be Dutch's tent. With him standing over them. Hiccup and Toothless came in the middle. And were in front of the group to hear what Dutch has to say.

"I know, that things have been tough these few days," he started. "But we are safe now, and we are far too poor. So it is time for everyone to get to work."

"Get to work, but stay out of trouble," Hosea added. "Remember, we are itinerant workers."

"Laid off when they shut down our factory to the North," Dutch pressed on. "Now, get out there and see what you can find. Uncle, Reverend Swanson, no more passengers. And you, Hiccup, I hope you don't follow their example."

Hiccup gave him a nod before he kept on listening.

"It is time for everyone to earn their keep," Dutch continued.

"There's a town way down the track called Valentine,"said Hosea. "It's a livestock town. All mud and morons if I remember right. That seems like a decent place to started."

"And uh," Pearson added. "We need food. Real food. That means every day, one of you go out hunting at least."

"And remember, whatever it is that you find," Dutch said as he pulled out a small wooden box and puts on top of a barrel. One of which takes an interest to Toothless. "The camp gets its slice. Now, be sensible out here."

And with that, everyone started to do their own thing again. But before Hiccup and Toothless were dismissed, Dutch called them both out one last time.

"And one last thing, Mr. Haddock," he said. "Keep your friend within the range of camp. I don't want anyone suspecting things while he's around."

"Okay," said Hiccup. "I'll keep in mind of that."

"Good," Dutch said as he entered his camp.

Then they both went over to do their own thing. And were on the road to prosper in this new camp called "Horseshoe Overlook."

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**And that wraps up another excellent chapter. Please click on the review box if you have anything regarding the story. Alright, stay tuned for the next chapter.**


	5. Chapter 5: Valentine

Hey** everyone. Here's chapter 5. Sorry for the long wait, but school just sin't kind to me. I just want to give a shout out to all of those who are following this story. It means a lot to have so many people reading this fine story. Okay folks, enjoy.**

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The shadows grew long as the sun rose from the eastern horizon. The trees above glimmered with rays that reflected though the time of dawn. The birds sang softly and flew through the divine winds. For young Hiccup, he was the first to awake from a long nights sleep. He stretched his arms and rubbed his eyes before starting the day's work. He first went for a sip of coffee to gain his senses. Then he started his first set of chores. He first grabbed a few sacks of grain and set them over near Pearson's station. Next he took some hay and took them over to the feeding posts near the horse. In which he greeted each one of them with a pat on the shoulders or a rub on the chin.

Next he picked up containers that were filled with water and placed them over to the station where the camp members wash their clothes. The last chore he did was chopping a few logs for the campfire, which was a chore that he mastered over the years. Time after time the gang members like Mrs. Grimshaw, and Pearson saw his work ethic and complimented his diligence.

It's been three weeks since he first found these people. And these were probably the easiest weeks he had ever had. The recent nights he spent sleeping with Toothless in his lap. Lenny and Charles offered him a spot at their tents, but he respectfully declined. He told them that he usually uses Toothless as a bed and has no trouble sleeping. And in their return, they understood his reason. But they also told him if he changed his mind, he could just say the word.

As the morning went on, he was greeted by different gang members. He was first greeted by Hosea and Karen, who called him a work horse for him to do all of his chores before anyone could do theirs. Next he was greeted by Mary-Beth, Tilly, and Abigail, who were impressed with his skills in a game of Dominoes that he played and won against Reverend Swanson the other day.

Later on, he was greeted by Bill, Lenny, and Javier who were kept rambling about seeing his fighting skills up in the mountains. And in which he told them that it was just something that his girlfriend Astrid told him. Once it was afternoon, Toothless was finally up. And he greeted him with the greatest of welcomes.

"Hey, good morning, bud," he said as he scratched the top of his head.

Toothless responded with a small moan before pushing his head into Hiccup's chest.

"Just got done with our daily chores," he told the Night Fury. "You wanna go for some exploring?"

Toothless nodded in excitement and was about to have Hiccup saddle him up. But before the young viking could do so, he was stopped by a sudden voice who belong to an old feller like Arthur Morgan.

"Hey Hiccup," Arthur called out.

"Yes Arthur," he responded.

He came to his right side with something in his hand. He didn't know what it was but was a bit interested.

"I just want to thank you for all that you did these last couple of weeks for this gang," Arthur started. "And, it return, I wanted to give you this."

He handed the item he had over to Hiccup, he accepted it and carefully examined it.

"What is it?"he asked him.

"It's a holster," Arthur answered. "It's a place where you can carry guns in such. I just thought that i could give it to you in return of your diligence around camp."

Hiccup kept examining it, and took a very good interest to it.

"I like it," he said. "So, if I were to head into battle, and I was to use something like this, where would it go?"

"Oh, that goes around your waist," Arthur responded. "Most gunslingers usually keep it there when fighting duels."

"Well," Hiccup said as he puts it around his waist. If fitted perfectly on him. One of which was the right size for him. "Well, that's kind of you Arthur. Thank you."

"Well uh, you wanna head into town with me and Uncle to see if we can find anything out?" the old gunslinger asked. "Perhaps even buy you a gun yourself."

"Sure," Hiccup answered. "I haven't even seen the town before so, why not give it a shot?"

"Good,"said Arthur. "Grab what you need and meet me at the wagons."

Then he walked away and into the woods nearby. Toothless looked at Hiccup and gave him a saddened look.

"Well," Hiccup sighed. "You know the rules bud."

Hiccup started walking off to the wagons before he felt a sudden nudge from his right shoulder. Turns out Toothless wanted to come too. But they both knew what they were told to do. Hiccup just needed to give him a little reminder.

"I know, Toothless," he started. "It sucks being cooped up around here. But Dutch told us that you had to stay hidden. And you know that we have to be loyal to him. But don't worry. The time will come soon. I promise."

Toothless looked down at the ground and looked back at him. Then he gave him a nod in understanding.

"Okay," said Hiccup. "I'll see you soon bud."

Then, Hiccup went to grab some things and headed straight for the wagons. Leaving a bored and sad Toothless behind. It was only a few more minutes before the three were ready. But before they could even get into their seats, they were stopped by a few certain individuals. More than likely Karen, Mary-Beth, and Tilly, who were sneaking about.

"If you're gonna take the old man in town," said Karen. "Could you take us along too?"

"Why?" Arthur asked. "What do you got planned?"

"Nothing," she answered. "We'll find something for y'all to do. We always do."

"We're bored out of our minds," Mary-Beth added. "Been cooped up here for two weeks now. Karen's about ready to murder Grimshaw?"

"Well, can Mrs. Grimshaw spare you?" Arthur asked.

The three women scoffed at his question.

"Can Mrs. Grimshaw spare you?" Karen mimicked. "What's happened to you Arthur. Three young healthy women want you to take'em robbing and you're worried about house chores. Let's go!"

Arthur thought for a minute before he gave them a nod.

"Fair enough," he said. "You got me. Come on then."

The three girls giggled before climbing in the back of the cart. Arthur got up to the front seat with Uncle and Hiccup and took the reigns.

"I can't wait to see civilization," Tilly gloated. "It feels like weeks since we did."

"Yeah, Valentine,"said Uncle. "The very embodiment of civilization. You ladies are gonna love it."

"Huh," said Hiccup. "I wonder what it's gonna look like since it's new to me."

"It should be plenty of fun here, Hiccup," said Mary-Beth. "I hear they have a farmhouse with lots of sheep in it."

"Now I can deal with sheep," Hiccup replied. "I use to be a shepherd when I was a boy. It wasn't a lot of work, but it was a handful."

"Okay then," said Arthur. "Let's go."

Then, he started the horses and the six of them rode off. Leaving the camp behind and with Toothless watching as they disappeared into the forests. They came out of the woods and followed the rode to a narrow path that lead right next to the Heartlands.

"Hey ladies," said Uncle. "Sing us a song."

They cleared their throats before they started singing.

"*_I got a girl on Berryville can't be screwed 'cause she's to damn ill_," they sang. "_So I don't go down there no more. There's a blue horse lays outside her door. I got a girl in Valentine likes to drink that fancy wine. Plumes in her hat was two feet tall the crack in her pants paid for it all. I got a girl in Berryville. Can't get it in her cause she won't stay still. She kicks and squeals and farts and hollers. Won't take less than seven dollars-"_

Then, before they could finish their song, a stagecoach just near them starts breaking off. And the next thing they knew, two of the carriage horses were loose from their harnesses and started bolting in different directions. Leaving the driver frustrated from this accident.

"Oh g*ddamn it," he ranted. "Oh sh*t, the horses!"

"Is one of you gonna go get that feller's hose?" asked Tilly.

"Oh I got lumbago," Uncle declined. "It's very serious."

"I'll see what's going on,"said Hiccup. "Just give me a moment."

He climbed down the seat and walked over to the stage coach. Arthur shortly followed him after, just so that he would look like he was actually helping.

"Lumbago," he mumbled. "Really."

They walked over to the man and asked him a few questions.

"Excuse me sir," said Hiccup. "You okay."

"Oh hey," the man started. "You two couldn't help me get my horses back from over there, could you? It's the one in the white and one in the brown."

"Sure," said Arthur. " No problem."

Then, the two walked over to the small meadow just across from them. There, they saw two work horses grazing in the fields.

"Okay," Arthur started. "You take the brown one I'll take the white one. Make sure you calm them before returning them to that man."

"Relax Arthur," said Hiccup. "This isn't the first time I did this."

"Okay. I was just making sure."

Then they both split up to go after the two horses. Arthur did his part fast and was able to get a hold of the reigns. Hiccup in the other hand, had a bit of a struggle since he didn't know much about horses. But with his knowledge of dragons, he began to manage. He approached the horse's hind side to avoid spooking it. Then he stuck his hand out as soon as the horse saw him and moved slowly towards it. He could already tell that it was a female due to it's size and facial expression.

"Easy girl," he said. "We're here to help."

Then, like any other dragon, he touched the tip of her nose and slowly grabbed the reigns. The he led the horse back to the stagecoach slowly. The others looked on and were marveled by the two fellers helping out some stranger. They both handed the reigns over to the man and he so kindly took them.

"You'e both gentlemen sirs" he said. "Gentlemen."

"No, not really," said Arthur. "I was just trying to impress the women."

"We're glad we could help,"said Hiccup.

"Well, anyway," said the man. "Thank you."

Hiccup gave him a little nod before going back to the wagon. Arthur followed him, and the two climbed up back to their seats.

"Come on,"said Uncle. "Let's go."

"To Valentine," the girls added as the giggled.

Then, Arthur took the reigns again and they were off to their destination. Yet, they were still marveled about their kind actions back there with that man.

"You're turning into regular old fair god mothers there Arthur," said Uncle.

"What's that suppose to mean?" asked Arthur.

"It mean you got a heart," Mary-Beth answered. "A small one perhaps hidden deep inside, but a real one."

"And you haven't you repulsive old lizard," Karen said to Uncle.

"Lizards have hearts," Uncle shot.

"And what about you, Hiccup,"said Mary-Beth. "You reckon you ever have a heart?"

"Well," said Hiccup. "To have a heart means you helping others in need of it. I was taught this when I was a boy. I always wanted to assist people. It's in my blood. And I will always keep helping."

"Well, I'm proud of you both,"said Tilly.

"To be honest, if you lot haven't been here,"said Arthur. "I probably would've robbed him."

They all laughed at those words. They knew that he was joking. Hiccup shot him a look before dropping it. He didn't take Arthur seriously since he knew that he was one for jokes.

They rode for a couple more miles before they finally arrived. And Hiccup was filled in awe with the scene. The town was almost like the one he first encountered, except it was a town that fitted his style. There were corals one the sides that they were coming from. And within those corals were filled with sheep. Lots and lots of sheep.

"Smell those sheep," said Tilly.

"Or is that Uncle," Karen teased.

The girls laughed at that joke. But Hiccup didn't really pay attention to that. He was instead looking at all the buildings and shacks that covered the entire town. And he was marveled about what the next generation of civilization would look like for him.

"Wow," he said in awe. "This makes all of the buildings and houses that I helped design at home look like...nothing," he muttered beneath his breath as he started beyond.

He looked at all the town people the passed by. Unlike the people in that previous town, he saw that these people had more of a rugged style in terms of clothes. And the women too dressed differently. Instead of them wearing colorful dresses, some wore the same clothing as the men did. Even the wagons looked somewhat different. They were more dirty and built to pull heavier things. Probably similar to the wagons he's seen back at camp.

"This looks like a decent little town," said Mary-Beth.

"Other people, said Tilly. "Finally. You think we should've asked Molly to come with us?"

"Oh no," said Karen. "Miss O'Shea is far to high and mighty for the likes of do any real work. She's a society lady now."

They traveled up a hill for a bit before they pulled into the main street. And from what Hiccup saw, was something that went up to a whole new level. It was a street that was covered in mud, and surrounded by even more buildings. The design was way off the charts. There were wagon, more hitching posts and much more. And at the end of the street, Hiccup saw a shack that had horses coming in and out. Which meant to be the stables in his mind. He loomed around nd saw buildings that were labeled many things. And all of them were free for Hiccup to explore.

"Oh, yes," said Karen. "We can get up to some mischief here alright."

"Just remember," Arthur reminded. "Keep a low profile."

"Will you be able to remember that though, Arthur?"

"Probably not."

They continued down the main street and eventually parked the wagon near a building that was under construction.

"Alright," said Uncle. "Here we are, just like I said. The cultural center of civilization. Man at his finest.""

"So guys," said Hiccup. "What are we doing first?"

"Well, we're gonna do what any self-respected maniac does," Uncle answered.

"And that's?"

"Put the women to work."

The women pretended not to hear Uncle talking.

"With pleasure," said Karen. "We'll start at the saloon."

"Alright," said Arthur. "Just stay out of trouble and don't get yourselves noticed."

Then the ladies started walking in the direction of the saloon. Leaving the three boys to do their own thing.

"I need to get something at the stores," said uncle.

"Okay," said Hiccup. "I might get some things too."

They started walking in the direction of the General Store. Which really wasn't that far from where they were going. In fact, it was probably two buildings to the left.

"So that's how you see yourself, is it?" Arthur questioned. "A maniac?"

"Well, in my youth I used to be know as the "One shot kid," Uncle explained.

"Okay," said Hiccup. "I'm not gonna ask why."

"Yeah," said Arthur. "I wouldn't even ask him anything."

"You're a sad man, Arthur Morgan," Uncle shot. "But I know you love me."

"Desperately," Arthur joked. "You're my favorite parasite. No, ringworm is my favorite parasite. You're my second favorite parasite."

"Very funny."

"I lied," Arthur added on. "Ringworm, then rats with the plague, then you."

"Shut up."

"Guys," Hiccup interrupted as he held the door open to the General Store. "Are we gonna buys something or bicker about it?"

They both stared at the young viking and pretended to not here him. For a moment, there was complete silence before they all went into the General Store. Inside, Hiccup was impressed with how organized the products were. Back at home, there was a number of organizing and arranging in their goods. Something that most vikings couldn't keep up with.

"So," Arthur said to Uncle. "What do you need?"

"Well, a drop of whiskey for a start," Uncle answered. "Something to pass the time while we're waiting on the women."

"Always thinking ahead, ain't ya?" Arthur commented.

"You're looking a bit tired there, Arthur," Uncle pointed out. "Why don't you take up some coffee while we're here."

"Sure," said Arthur. Then he turned over to Hiccup, who was browsing through the items.

"You need anything kid?"

"Well," Hiccup started. "Probably something to keep Toothless fed. He goes really heavy on fish."

"Okay," Arthur responded. "Well, I'll meet you outside when you'e done."

When Arthur and Uncle were done buying their things, they went outside and sat o0n the benches. It didn't take Hiccup long to find what he needed. He placed a few things on the counter and the shopkeeper expected each one. What he had was a few items. Those included some fruit, some tools for his saddle and armor. And the last thing was a few frozen fish for Toothless.

Once he was done, he used some of the money he had from the train robbery to pay for the items. After he was finished, he put those items his satchel and joined the other two outside. He sat on the benches and waited for the women to be done with their work. This was a very strange place to him. It was something that he thought of as he was waiting.

He thought of how civilization changed so quickly in this world. He thought of the buildings, And it might add in a few ideas for home. But he just had to get back. Which was a real problem. With those men after them, there's no chance in flying out. And for what these guys did for them, he wouldn't turn away from them either. Dutch saved him and Toothless in those mountains. And they owe him greatly.

About an hour later, they were still waiting on the women. Arthur and Uncle fell asleep while he kept watch. He kept waiting until from the corner of his eye, he saw Mary-Beth coming out from the saloon and headed towards them.

"Gentlemen," she greeted.

"Mary-Beth," Hiccup greeted back. "Did you find anything interesting?"

She looked around to see if anyone was hearing before finally breaking the news.

"I think I got something good," she said.

By the time she said that, Arthur and Uncle had already awaken.

"I snuck into this fancy house," she explained. "Acting like a servant girl. It usually works."

"Okay," said Hiccup. "What did you find?"

"Someone was saying her sister was taking a trip from New York or some place," she continued. "Train full of rich tourists heading to Saint Denis and then cruising off to Brazil."

"Okay," said Arthur.

"What's so important about that?" asked Hiccup.

"A train laden with baggage and passing through a bit of deserted country through the night as to get to the docks in time for the tides in some place called "Scarlet Meadows."

The three gentlemen had to think for a moment. But it didn't take Uncle long to figure it out."

"Yeah, I know it," he said. "Yeah, yeah, it's right out in New Hanover. Right, it's real quiet out there."

"Sounds good,"said Arthur.

"Hey," said Hiccup. "Where's Tilly and Karen?"

"I think at the hotel," she answered. "They were picking up some drunken fellers that they was gonna rob."

"Why?" Arthur questioned.

"It seemed easy," Mary-Beth answered. "But I'll admit, they have been gone for quite a while."

it was then Hiccup and Arthur started to worry. If they were gone for a while, then that means there's trouble.

"I guess we'll go see if there's any trouble," said Arthur. "Hiccup, you go look for Tilly. I'll see what Karen's up to."

"Alright," said Hiccup. "We'll be right back."

Then they were on the move. But before they could even take a step. Mary-Beth spots something.

"There's Tilly over there," she said as she pointed at the other side of the street. They saw Tilly being dragged over to the corner by some stranger. Which meant trouble. "That does not look ideal."

"Excuse me," Arthur said as he walked over. But before he could get any closer he was stopped by Hiccup.

"Arthur," he started. "Let me take this one. You go check the hotel and see where Karen's hold up."

"You sure you're up for this?"asked Arthur.

"Why wouldn't I be," Hiccup answered. "I'm always up for helping friends. No matter how big or bad they could be."

Arthur thought for a moment before he finally granted his request.

'Fair enough," he said. "You go make sure Tilly ain't hurt. I go in the hotel after Karen."

"Okay. I'll see you in a bit."

Then, Hiccup walked over to the other side of the street and went straight for the man who was with Tilly. He seemed to be harassing her in a non-gentle manner. Which made Hiccup determined to break it up.

"Hey," he called out. "I think it's about time you left the lady alone."

"Who are you?" the mysterious stranger asked.

"A friend of mine," Tilly answered.

"Yeah," Hiccup added. "So I suggest that you let her go and get out of here while you still can, before things start to get pretty ugly."

The stranger lets go of his hold on Tilly and confronts the young viking.

"Or what exactly, boy?" he questioned.

Hiccup puts his hand on the top of his swords as if he was gonna draw. But doesn't quiet do so. As if it was a warning.

"Wanna find out,strange hostile person whom I never met?"

The man had to think for a moment. He saw that the boy wasn't playing around. A fight like this would alert every person in town. Which was something that neither of them would want.

"You're making a big mistake, Tilly Jackson," he said.

"Just get lost," she shot.

Then, he turns to the other corner and leaves the two to themselves.

"You okay?' Hiccup asked.

"Yeah," she responded. "I'm fine. Thank you by the way."

"Well, that seemed a bit nasty," said Hiccup. "Come on. I'll take you to the wagon with Uncle and Mary-Beth."

And like any other gentlemen, Hiccup took her hand and walked her across the street. When they got there, they waited for Arthur to come back with Karen. It didn't take him long to find her. Cause after about a minute or two, he came out of the hotel with Karen behind him. The chief saw that she had some bruises on her face. But he didn't reckon he should ask her why.

"You okay?" Mary-Beth asked her..

"Sure," she answered. "He only punched me. But Arthur punched him a lot harder."

"Well,I'm just happy that you're okay," said Hiccup.

"Thanks, Hiccup," said Karen.

Then Mary-Beth saw something very strange that came from behind Arthur.

"Hey," she said. "Who's that guy over there looking at us?"

They looked behind them and saw a man on his horse just looking at them. He didn't seem much to look at, but it was very suspicious.

"Weren't you in Blackwater a few weeks back?" he asked.

"Me?,"said Arthur. "No sir. I ain't from there."

"Oh you were," said the stranger. "I definitely saw you with a bunch of fellers."

"Me? No. Impossible."

Then Hiccup started to get nervous. For someone who can already tell who they are would mean extreme exposure.

"Listen buddy," said Arthur. "Come here for a minute."

"I saw you," the man repeated.

"Come here!" Arthur demanded.

The man started to panic. He turned the other way and started high-tailing across the farms. Now they were into some real trouble.

"I don't like this," said Uncle

"Me neither," Arthur responded. "Go get the girls home. I'm gonna go have a word with our friend."

"You want me to come?" Hiccup asked.

"Nah," Arthur answered. "I got it from here. You go meet me at the Gunsmith later on. We still got that gun that I owe you."

"Okay," said Hiccup. "Be careful Arthur.

"Just a word."

Then, he mounts the nearest horse and goes after the mysterious man. Leaving the others behind in the process.

"Okay," said Hiccup. "Shall we?"

Then they started loading the supplies for the trip home. It didn't take them long to load the wagon. By the time it was evening, they were packed up and ready to go back home. Hiccup lent Mary-Beth his satchel and told her to give it to Toothless. She would ask him why, but she already knew what was in it.

"Alright lades," he said. "Uncle. I'll see you all back at camp."

"You're no coming along?" asked Tilly.

"No," he said. "I've got some business to do elsewhere. It shouldn't take me long."

"Alright. But, thank you for what you did back there."

"I was glad I can help. Y'all take care of yourselves now."

"Okay," said Karen. "It was fun riding with you."

"Same as you," said Hiccup. "I'll see you later."

Then, with a wave of goodbye, he watches as the wagon along with Uncle and the girls take off and back to camp. He watched as it disappeared into the hills, leaving him by himself. Then he started walking down the main street in hopes of exploring the wondrous place of Valentine.

* * *

**Alright everyone. That's the end of another chapter. Please click on the review box bellow if you have any questions, concerns, comments, suggestions or just in general for the story. Okay, stay tuned for the next chapter.**


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